50 Shades of Cowboy
by LovelyFangirls
Summary: Castiel isn't familiar with gay sex, and decides Dean should be the best tutor, sharing a 'more profound bond' and all. So Dean agrees to teach him, but what starts as a few simple kisses has the potential to turn into- well... I'll leave the rest to your imagination. M FOR A REASON OBVIOUSLY! Destiel/Sabirel (language, smut and such) some things subject to change.. Sorry its short
1. Be a Cowboy

"Dean?"

The eldest brother looked up from his dinner to see the familiar angel right in front of him. He roamed his eyes awkwardly over his body before stabbing another mouthful of pie. "What is it this time Cas?" he asked, raising the pastry to his mouth.

"How do two men have sexual occasion?"

Pie and saliva shot from Dean's mouth. "Wh-What the hell Cas? Why would you ask me something like that?"

Dean gathered up a stray napkin off the large table in their bunker, trying to wipe away his spit take. Sam would have a girly fit if he'd left a mess. Cas frowned before replying, "I'm aware of how a male and a female interact, but I don't understand how two men go about it. I figured that since you've had vast experience with sex, you were the one to ask."

"H-How did this even come up? Did you just wake up and think, Hey! I wonder what gay sex is like?" Dean flitted his hands about mockingly, making a funny face to accent his cruel act.

The angel wasn't amused. "Gabriel and I met the other day and he told me that Sam was a sex god... and... he spoke from personal experience." His innocence almost insulted Dean, who's mouth was open slightly.

"Wait, wait, wait... Sam and Gabriel are goin' at it?!"

"Yes." he replied bluntly.

Dean swept his hand over his face, "Seriously?" he gave the angel another awkward glace before continuing, "Well... umm... what exactly did you want to know about it?"

"Well, where does the man put it if not in a woman va-"

"Alright, alright." Dean held his hand up defensively, "More then needs to be said man."

Castiel stayed silent, waiting for reply.

"God this is awkward man... why didn't you just ask Gabriel? Or Sam even!?"

"Gabriel left on important business, and I didn't want to alarm Sam."

"Oh, but freaking _me_ out was just fine?" Dean spat, irritated.

The angel looked distressed, "Well, you and I do share a more profound bond. I thought you'd understand."

"Yeah well I-"

Dean stopped himself when he caught a glance of Castiel's expression. He looked like a lost, helpless puppy looking for a way home. He shook his head, "Alright. I give up."

Cas perked up instantly.

"Well, see... instead of... the woman's part, the guy sticks it in the other guy's ass." he explained, very stressed with the entire situation. "That's basically it."'

"But, doesn't that hurt?"

"I guess... But! There's this little sweet spot hidden in there. If your partner hits it, it's the extreme gay ecstasy."

Castiel took the seat just in front of Dean, propping himself up on his elbows, which rested on his knees, "So, if men can have sex with one another, are there other things they can do that would normally be done with a man and a woman?"

"Like what?"

"Reproduction?"

Dean laughed, "No man, there's no where to knock up a dude if that's what you mean."

"Kissing?"

"Yeah, that's a given."

Castiel seemed unsure of his next question, "...Does it feel good?"

"What? Sex?" Dean asked, smiling to himself when the angel turned red.

"N-No... I meant kissing..."

That cheeky Winchester smile popped up, the one that makes their entire reputation seem childish and silly. He looked smug. "Well, I can't really say. It's different for everyone, just depends on the person kissing and the person who gets kissed. And experience is key. Practice is what makes it all worth while." he closed his sentence with a short wink.

What a tease.

Cas innocently nodded, "So, then _you_ have experience?"

"Loads."

There was a short period of silence while the angel pondered what to do, "Would you kiss me?"

Dean felt a surge of unhealthy power flow through him, and he decided to push it a little further, "Why?"

"Because I want to know what it feels like." he replied, his face still tinted with reds and pinks.

"Well then, I'd like some compensation for my troubles."

"Like?"

Lifting his arm, Dean gestures for Cas to stand, rolling his wrist in motion to come forward. Cas is standing right before the man now, their knees bumping lightly. Dean tugged at his trench coat sleeves, dragging the angel down to sit on his lap. Cas started to Dean's side, ready to sit, "No, not side saddle."

"Side saddle?'' he asked.

"You know, like riding a horse? It's usually a woman, but when they have both legs on one side it's called 'side saddle'."' Dean explained, before being irritated with himself for knowing something like that, "Damn it Sammy." he muttered.

The angel furrowed his brow, "How should I sit then?"

"Straddle me Cas." he grinned, "Be a cowboy."

"Strad-"

"Legs on either side. Facing me."

Castiel was hesitant, his fingers fiddling with the hem of his coat for a few minutes before he finally worked up the courage to climb onto the hunter's lap. He placed his hands cautiously against Dean's shoulders, his eyes drifting from one section of Dean's face to another numerous times. "Calm down Cas."

"I am calm."

"You're shaking." he chuckled.

"I'm sorry... is it bad?"

"No." Dean smiled, reaching a hand up to the angel's cheek, "It's cute."

Castiel's first kiss was soft and gentle, a firm hunter's grip on his waist. His second was just as sweet, but lasted a fraction of a second less then the first, but was longer then the third. The fourth was a bit more rushed, a little more urgent, but not in the least bit disappointing. Dean was pulling at the angel's coat now, inching him closer every time their lips connected.

When the two drew back, Dean searched Castiel's eyes anxiously for feedback. In kind, the man wrapped his arms around Dean's shoulders, burying his face in the crook of his neck. The angel's stubble tickled, and he couldn't help himself from chuckling, "Hey, cut that out. C'mon look at me." he urged.

Cas's grip tightened as he shook his head, "No."

"What? Why not?" Dean was worried that the kiss was awful.

Instead, he found himself smiling, "I can't look at you... My face is too hot... It's embarrassing."

Chuckling again, the Winchester pushed at Castiel's arms, forcing them to be face to face, "Cas." he grinned, "I already told you." He led the stubbled chin in once more for another kiss, "You're adorable."


	2. My Angel

Before the angel's head caught up with his body, he was already rolling his hips. The delicious sensation of Dean pressed against him was a new found intoxication that left them both with racing hearts. Dean was pleasantly surprised when Cas started responding this way, and maybe a little more aroused of it then he should be over a man. However, his body begged to respond, seemingly not caring that it's target was a man. He nipped at the angel's neck with short pecks, sneaking his hands beneath the big trench coat and running them up Castiel's naked back. His skin was warm and addictive. Cas hadn't been expecting Dean on his neck, and whimpered unintentionally as he turned his head to give the hunter more access, more on basic instinct then strategy. When Cas's hip movements slowed, Dean took the initiative, pulling him by the knees, "Lock your ankles behind me." he ordered.

The angel complied, his arms clinging desperately to Dean's back, head tucked in the crevice of his neck. Dean stood, supporting Castiel under his thigh and making way to his room. He was painfully hard, trying to walk carefully so as not to drop his partner. Cas was smiling. Most people wouldn't think smiling was a big deal, but for Dean to see this straight-faced-n-constipated angel to smile the way he did, made his heart skip. Hell, the last time Cas had smiled was when his vessel had been introduced to hamburgers. Castiel, was smiling because his mind had kicked into play, staring at the hunter's neck and deciding how to go about it. He shifted a hand from Dean's back, pulling the savory neck closer before nibbling lightly, experimentally. When Dean reacted, Castiel was tremendously pleased. Dean picked up his walking pace, dying to make it to the damn bed already, "You'd better cut that out, I'll end up dropping you!" he warned, "God damn tease..."

Castiel pulled away, giving Dean a worried look, "Did I do it wrong?"

He looked like a lost puppy, "N-no... It was really good. It's just distracting."

"Is distracting bad?"

God... it wasn't fair that this guy was so innocent, his little virgin mind with his adorable virgin questions was driving Dean crazy. He swore over Castiel's blue eyes before planting a soft kiss on the angel's lips. He was starting to think he'd come before they even reached the bedroom, "This place just needs shorter hallways." he replied, irritated.

Finally, they reached the end of the hall, Dean kicking his door open with excitement. The kissing restarted before they reached the bed, Cas moaning seductively into the hunter's mouth. Dean lopped his knee onto the edge of the bed, crawling forward as he lowered the angel onto his back, taking place between his legs. The trench coat was first to fly behind them, finding place on the floor before other discarded clothes joined. Dean waited before pulling off the angel's trousers, savoring the sight of a blushing, shirtless angel. Cas pulled his hand up to cover himself, "Don't stare. It makes me feel uncomfortable."

Dean towered over the angel, grinning, "Why is that?" he cooed, leaning down slightly in seek of more neck.

"I-I don't know..." he whimpered.

Dean spoke into his partner's neck, "As adorable as it is, I need to move them out of my way."

"Your-?"

Dean took firm hold of Castiel's wrists, lifting them up above his head. He locked them against the bed sheets before retiring to the angel's lips once more. Satisfied, he started on a nipple, boiling over with pleasure when Castiel arched to meet his mouth. More delicious whining noises were rewarded for his hard work. The hunter shifted both wrists into one powerful grip, his other hand snaking it's way down the side of Cas's naked body, pushing down the unwanted pants. Dean smiled when he noticed his angel writhing beneath him, those seductive hips rolling all on their own.

He quickly climbed out of his jeans, frustrated things were progressing so slow. Not that they really were, but... his erection ached, begging for attention. He shouldn't rush this... Cas was a virgin after all, but... the way he was looking up at Dean, innocently, head cocked to one side, cheeks a rosy red, arms trapped above his head as his legs twisted about in petty attempt to hide his nakedness... well, it would drive any man insane. He was giving into it gladly. Dean returned to the plush lips, proud of how swollen the already were thanks to him. He drew back with a sudden snap, grinning maliciously before continuing his endeavors.

Castiel tried not to cry out when his erection was grasped, but failed miserably. He was starting to get the impression Dean loved his noises, but that thought only made him more embarrassed then he already was. He'd never actually been this naked by himself, let alone with someone else over him. However, Castiel was happy it was Dean. He'd admired Dean for the longest time, his bravery, his caring heart. There was a reason he'd been pulled from hell. Castiel's eyes searched, looking for the scar, his imprint on Dean's arm. After finding it, he tried to grasp it, only then remembering his bonds. This hunter was giving Cas sensations in places he didn't know could create them. His rolled his head back, his breathing chopped and unnatural as the hand's pace quickened.

Dean was holding back with every ounce of self-control he could muster. His angel was... his angel? Dean's head trailed off into other thoughts as he looked at the man beneath him. _His _angel? He was called back to attention when his hand became warm and wet. Castiel's cheeks were the reddest he'd ever seen, nearly gasping as he looked at Dean with lidded eyes. Dean smiled to himself before rolling to the side. Cas was already worn out, he didn't want to push it. It was only a brief moment before he felt warmth against his side. Cas had snuggled into him. Dean wrapped a protective arm around the angel before ghosting a soft kiss over his forehead. _My_ angel.


	3. Author's Note

**Sorry to end this story here, there were just other prompts I need to finish/put up. I may decide to add to this later, If I do, I'll notify everyone who favorite it or followed it. Apologies, but there's too many ideas floating around in my head and not enough hand power to type them all out. **

**Thanks for my loyal supporters who came to read this little smut ;) (They read/comment on MANY of my stories) **

**-Sherlockiannightmare**

**-Dr. Kaitie Holmes**

**-CastiellaWinchester94**

**Love you all! Thank you for your continued support!**


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